The Great Canoe Race

Across six months, five islands and four ocean channels, Hawai‘i’s canoe sailors set a course for adventure.


Catharine Lo

canoeTom Boomer’s first harrowing experience at sea happened when he was barely a kindergartener. From four inner tubes and some two-by-fours, he fashioned his first boat, perfect for exploring the watery playground in his Tiburon backyard. He was four, and his neighbor, he remembers, was five. The two young boatmen had to be rescued before they floated out of San Francisco Bay into the wide, wild Pacific.

Over the years, Boomer has sailed “just about everything that floats.” The late 1960s found him navigating motorboats for the Navy in Vietnam. Fast-forward another two decades, and he was at the helm of a Hawaiian sailing canoe, racing across the Pailolo Channel from Maui to Moloka‘i.

Side by side with Captain Mike Kincaid’s canoe, Boomer recounts how each tried to scoop the other’s wind line. As Boomer passed on the inside, he also passed over the tail of a full-grown bull whale. “It waved and slapped its tail a few yards away and our ama [outrigger] went flying,” he says, his eyes opening wide with the memory. “If he’d hit the boat, we’d have turned into splinters. That tail had to be as long as the ama—which is twenty-seven feet!”

Boomer’s story echoes those of his fellow canoe sailors, the unsung roughriders of the Pacific who love to pit their navigational skills against each other and the unruly sea. They relish the thrill of harnessing nature’s might, the narrow escape from a hairy predicament, the camaraderie created in pursuit of a daunting, singular task, and the nostalgia of looking back at those moments and realizing that they are among the most priceless of your life.

“It was 1987, the Year of the Hawaiian,” Boomer says, recalling the beginnings of the Hawaiian Sailing Canoe Association. Sailing canoes are modified six-man outrigger canoes with an additional ama and a sail hoisted on a mast between the canoe’s first and second seats. They’re modeled after traditional Hawaiian sailing canoes (the ancestors of modern-day catamarans) that were used in old Hawai‘i for fishing, racing, interisland transportation, and long-distance voyaging. The vessel is steered with an oversized paddle from the back seat, and its sail trimmed from a trampoline that connects the outrigger to the canoe.

Kaua‘i’s Nick Beck won Na Holo Kai, the first sailing-canoe race from O‘ahu to Kaua‘i, twenty-one years ago. The HSCA has since expanded its contest series to an annual chain-of-islands race that begins on the Big Island, crosses each of Hawai‘i’s notoriously unforgiving channels, and ends on Kaua‘i. The race takes place over the course of six months from April through September, with thirty-day stops on each of the major islands during which the public has a chance to learn about the tradition of sailing canoes. The distances range from 15 to almost 100 miles, all human-powered and navigated without GPS.

In the second race in 1988, Maui watermen Cappy Sheely, Mike Spalding, and Eric Bartow decided to enter a crew. The sheer endurance of their paddlers helped them prevail in extremely light wind conditions.

“Cappy Sheely set the bar. You’d come in and he’d be having a beer already,” remembers Kaua‘i’s Marvin Otsuji, a veteran of all twenty-one HSCA races.

With top physical conditioning, ocean knowledge, and mental strength, the Maui crew maintained the pole position for the next four years. Sheely, who learned to steer from Hawaiian Olympian Duke Kahanamoku, attributes his team’s success to the “total package”: a masterful steersman who can read the swells, a sheetman who knows how to trim the sail for maximum wind speed, a properly maintained canoe, and dedicated paddlers with physical and mental stamina. They all have to work together effectively, he adds.

“A good crew will catch a wave a little sooner and stay on it a little longer,” Sheely says, explaining that every little bit helps, especially when such long races—ninety-four miles from Hale‘iwa, on O‘ahu’s North Shore, to Kaua‘i’s Nawiliwili Harbor, for example—can be decided by a matter of seconds. Indeed, on Otsuji’s eighth try, his boat beat Sheely’s by a scant twelve seconds in the last 200 yards of the race.

“I caught a wave, and he missed it,” Otsuji recalls. Otsuji, the undisputed captain to beat ever since, selects his crew not just because they’re great athletes, but because they have the mental toughness that the grueling channel crossings require. “These guys will be paddling for six to eight hours. They have to know how to pace themselves. They have to have that drive,” he says. “They may not be the best paddlers, but they’ve got the heart. They’re gonna die before they give up.”

Tom Boomer agrees. He illustrates the challenge with concrete numbers: The weight of the canoe and all its gear is about 800 pounds. Add six healthy paddlers, and you have the task of pushing 2,000 pounds at fifteen knots through some of the most merciless ocean conditions in the world—without a rudder or keels. “This is not a sport for the timid,” Boomer states. “Once you get in that canoe, you’re in it. I have seen people, including myself, who have paddled more than ten hours straight. It’s an extreme sport. There is no relief.”

Indeed, canoe sailors are watermen and waterwomen who have been involved in ocean athletics most of their lives, many of them local legends in their own right. Most come from a paddling background and enjoy team sports and competition. Sage Spalding, an avid paddler and former longtime sailing-canoe racer who now operates Hawaiian sailing-canoe excursions in Wailea, offers some insight into the sport’s prevailing attitude. “Anytime there is more than one sailing canoe in the water,” he says, “it’s always a race!”

The thrill of competition, however, is often surpassed by the fear-fueled adrenaline that accompanies close calls at sea. Sage remembers an instance when his crew was caught by a mast-high wave outside Waimanalo, on O‘ahu’s windward coast. The wave broke on their stern and flipped the canoe (the Kukulu O Hina, built by his brother, Sark Wetzel) end over end.


“The canoe got stuck upside down with the mast sticking in the reef. Every time a wave would pass, the canoe would get high and dry. We had to swim under with no mask or fins and cut away all the rigging and sail, while one of us swam around and retrieved all the surfboards, fishing gear, coolers, beers, paddles, you name it,” Sage remembers. “Over the next four hours we finally drifted close enough to shore where I had to swim in—I lost jun ken po [island-style paper/scissors/rock]—and hitchhike back to Sark’s to get the truck and all the tools.”

Boomer rattles off his share of misadventures: “I’ve crashed the canoe on a reef on Moloka‘i. I’ve crashed on Shipwreck Beach [on Lana‘i]. I’ve had my mast come apart. I’ve had my sails blow off.” In such situations, there’s no time to be afraid, he says. “If you are, you’re dead.”

Thirteen years ago, the race was called off because it was too windy, but the maverick sailors decided to go anyway. That year, master paddler Gaylord Wilcox was bounced off his canoe and spent five hours floating in the middle of the ocean until a sailboat fortunately discovered him.

That same year, Marvin Otsuji found himself swimming to Lana‘i with his crew after the wind broke his ‘iakos (outrigger booms) off the canoe. He says that night they made a fire from the masts, which had drifted to shore. Nobody knew they were missing. “We were kind of shipwrecked in Hawai‘i, and no one could find us, so that was kind of funny,” he says, looking back at the situation lightheartedly. The Coast Guard began searching for them just before midnight and found them the next morning.

Such experiences have helped the HSCA develop a strict set of safety regulations. Crews now have escort boats, and the canoes carry EPIRBs (emergency-position-indicating radio beacons), GPS devices, cell phones, marine radios, life jackets, smoke flares, strobe lights, whistles, spare paddles and other tools that will keep them as far out of harm’s way as possible.

The uncontrollable variables inherent in setting out to sea will always remain, but the sailors readily accept the risk. “Where else in the world can you do this, go from island to island in these primitive vessels?” asks Marvin Otsuji. “Afterward, it takes me a week or so to get my body moving again. And we think it was fun, and we keep coming back.”

All-around Maui waterman Mike Spalding (who swam across the Moloka‘i Channel last year) explains why. “We’re all fun hogs. For us who grew up doing water sports, it’s like insider knowledge that canoe sailing is the most fun you can have in the water in downwind conditions. It’s amazing to go that fast, surfing big, open-ocean swells, having waves crashing over you and trying to avoid getting slammed,” he says with a big grin. Spalding’s attitude represents the waterman’s unspoken credo: “If we go down, we’re not gonna go down crybaby sad. Reality is in the moment. We’re gonna go down happy.”

How to Participate

Join the Hawai‘i Sailing Canoe Association for a free canoe clinic on Saturday, May 31. Before the Maui-to-Moloka‘i leg of the race, the canoes will rest on Ka‘anapali Beach, and the HSCA invites the public to experience twenty-minute sails along the shoreline. The animated canoe sailors will gladly regale you with recaps of their adventures at sea. The community event is sponsored by the Ka‘anapali Beach Resort Association.

Throughout the year, Sage and Liz Spalding offer two-hour sailing-canoe excursions from Polo Beach (fronting the Fairmont Kea Lani) in Wailea. In this delightful variation on the typical snorkel tour, passengers have the option to dip a paddle or simply kick back and relax on the trampoline. For information, call Hawaiian Sailing Canoe Adventures, 281-9301 or visit

Canoe Clinic

What: Free sailing-canoe rides (weather permitting) and cultural information sessions
When: Saturday, May 31, 10 a.m. –  2 p.m.
Where: Ka‘anapali Beach in front of the Whaler condominium
Who: Adults and children eleven or older accompanied by adult. (Child-sized life vests will be provided.)

2008 Race Schedule

Hawai‘i Island to Maui • April 19–20
Maui to Moloka‘i • May 30–June 1
Moloka‘i to O‘ahu • July 12–13
Na Holo Kai, Hale‘iwa to Nawiliwili • August 9
Kendall Pacific Classic, Nawiliwili to Waimea • September 13


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